The First Shipper
by acertainzest
Summary: Roy Montgomery was shipping Caskett before they even met. Based on a twitter conversation and posted for CastleFanficMonday.


_**Author's Note:** To all who are waiting for the next installment of The Life Of Sound, my apologies. I spent most of the weekend in bed with a cold and was not able to bring the next chapters up to my acceptable standards. I promise to have an update for that story very soon, hopefully tomorrow._

 _Meanwhile, for CastleFanficMonday, here is a little piece based on a recent Twitter conversation - the gist of which was that Captain Montgomery was plotting to get Castle and Beckett together even before she caught the Tisdale case in the first episode. I hope you enjoy it._

* * *

Roy Montgomery is a tight-lipped kind of guy. He knows what to say and when, but more, he knows when to shut the hell up. It's what made him a great detective; it's what makes him a great police captain.

It also makes him a good poker player: he knows when to hold 'em and when to fold 'em. And when his boss the police commissioner says "Bob's inviting a new guy to join us at the table this weekend," Roy knows better than to say anything other than "Okay." Especially since Bob is, of course, the mayor.

Roy knows enough to keep his opinions to himself when it counts, like those first few poker games with this new kid, the mystery writer, Rick Castle, who Roy thinks is kind of an asshole at first. The commish and "Bob" clearly think highly of the kid, so Roy is happy to keep his poker face on and take the guy's money.

It doesn't take long, though, before he starts to see what the other men see in Castle; to see through the facade. Behind the brash, arrogant mask that the guy wears, behind the braggart and the clown, Rick Castle is actually pretty smart and an interesting guy, quick-witted and entertaining. And, after Roy breaks down and quietly gets himself a copy of one of Castle's books, he has to admit that the kid is a pretty good writer too.

So, slowly, he warms up to Castle, and the poker games are fun again. Like the rest of them, Castle is a decent player, has his good days and his bad days, both of which he accepts with equanimity. They all rag on each other constantly, the trash-talking an integral part of the game, and Castle gives as good as he gets, always with good humor.

But one evening, he's having a particularly bad run, and the others around the table - the mayor, the commissioner, a couple of judges, the assistant D.A. - are giving Castle a lot of shit tonight. His smile is getting a little strained around the edges. Roy, as usual, keeps his mouth shut except for the occasional friendly jibe.

Then the mayor lets loose with "What's the matter, Ricky, divorce making you soft? Is it finalized yet?"

"Yeah," Castle says, tightening his lips as he pushes some more chips into the pot. "It's final."

"Ooh," says one of the judges, with genuine sympathy this time, patting Castle's shoulder. "Sorry about that, kid."

"Nah, it's fine," the writer replies, glancing around the table. "It was doomed from the start, to be honest. I still have to work with Gina, but hey, at least I don't have to listen to her any more." And he smirks that obnoxious asshole smirk, which at first Roy found incredibly irritating, but by now he has figured out that it's part of the act.

The guys around the table chuckle appreciatively at the joke, and the game moves on, but Bob is still stuck on the topic of Castle's love life.

"So, you're single again, huh, buddy?" he prompts. "How's that workin' out for you?"

"Plenty of fish in the sea," Castle says, deflecting, but the commissioner picks up the thread.

"You know what your mistake was, Ricky," the commish says, pointing a finger at the guy, "was marrying a creampuff like that. All wrong for you. Too soft."

"True. True," Bob agrees, nodding thoughtfully. "What you need is a girl who can kick your ass." Chuckles all around the table, and nods.

"Yeah," agrees one of the judges, "keep you in line. A tough, badass kind of chick. And tall," he adds, because Castle is taller than any of them, and they all nod at that too.

Roy nods along with the rest of them, noncommittally, because until this moment he has had no opinion whatsoever on Castle's love life. But all of a sudden he finds himself thinking about Beckett.

Kate Beckett, his star detective. A tough, badass kind of woman if ever he saw one. And tall.

Once the idea has taken hold, Roy can't let it go. It nags at the back of his mind for weeks. The more he thinks about it, the more sense it makes. Beckett is way too serious; she needs someone to lighten her up, and although she jokes around with her junior detectives, that doesn't really cut it. That's just normal cop stuff. She needs someone to be truly silly with. And Castle needs a woman who will, as the mayor said, kick his ass, make him behave, maybe make him grow up a little.

Roy is pretty sure that Beckett is single right now. As far as he knows, she hasn't dated anyone since the disaster with that Fed, Sorenson. Roy doesn't know exactly what happened there, and it's none of his business, but the Fed got transferred to another city and it's quite obviously over. Good riddance. The guy was _boring_. Beckett deserves better.

Still, even assuming that she is single, and knowing that Castle is as well (notwithstanding the occasional one-night stand), Roy can't figure out how to get the two of them together. It's a delicate situation. He's Beckett's superior officer, so any direct attempts to meddle in her personal life would be grossly inappropriate.

He contemplates inviting her to join the poker game, but that seems iffy. Beckett is pretty unflappable, but even she would probably feel a little intimidated by this crowd: her boss, her boss's boss, the mayor, the judges. And she would likely be the only woman present (one female judge does join them on occasion, but her schedule is erratic). No, that would not be the best environment for Beckett to meet Castle for the first time.

A few months go by while Roy is still mulling this over, unable to think of a good way to get the two of them into the same room. And then fate, if you believe in that kind of thing, takes care of it for him.

"Where's Beckett?" he asks one morning as he enters the 12th Precinct, and Esposito tells him that she has gone to collect some evidence.

"I don't have time to wait for her to get back," Montgomery says, "so give me the run-down on the Tisdale murder." The latest victim is the daughter of a prominent businessman, so Roy knows that he's going to start getting pressure from above to wrap the case quickly.

"Beckett brought in a person of interest last night," Esposito says, "some writer, uh, Castle?"

"Rick Castle?" Roy exclaims, feeling his poker face slip for just a moment. Espo nods.

"Yeah, uh, apparently Beckett recognized the staging of the murder scene, like something out of this guy's book."

Roy goes to sit behind his desk, his thoughts whirling. Truth be told, he's a little disappointed that he didn't get to witness the first meeting of these two - but even more interesting is the fact that Beckett recognized the crime scene. That means she has read Castle's books. Oh, this is good. This is very good.

He picks up his phone and dials.

"Castle."

"Hey, Rick. Roy Montgomery. I hear you paid a visit to my shop last night."

"Hey, Cap'n! Yeah, sorry I missed you, but tell your guys thanks for the hospitality," Castle jokes.

"I will," Roy grins, and adds, "So, you met my star detective. I hope she didn't bust your balls too hard."

"Oh, she was awesome," Castle gushes, and he actually sounds sincere. A flutter of hopeful excitement rises in Roy's gut. "I never got hauled in for questioning about a murder before, that was so cool," the kid goes on, and Roy shakes his head. But that kind of enthusiasm is exactly what he has been appreciating in the guy, isn't it?

"So, about this murder based on your books," Roy prompts, and deftly, skillfully, he plants a seed of an idea: that Castle should assist with the investigation. Within a few more minutes of careful conversation, he has Castle entirely believing that the whole thing was his own idea.

Half an hour later, when Beckett returns with boxes full of Castle's fan mail, the man himself is already in Roy's office, chatting casually about the Knicks. Roy calls Beckett in and tells her that Castle has offered to help.

"It's the least I can do for the city I love," Castle says sanctimoniously, and Roy keeps his poker face on, concealing his glee. Oh, the kid is entirely snowed.

He's gratified to see how much Beckett hates the idea. It's exactly what he expected. This is going to be _fun_.

"Sir," she demands angrily, "can I talk to you for a minute? In private?"

"Nope," he replies happily, and leaves them to it.

Somewhat to his amazement, they turn out to be a good team. They solve the case together, and although he can tell that Beckett is still frustrated and annoyed by Castle about 99 percent of the time, he can also see that the guy is already having a positive effect on her. She's thinking more creatively, honing her already sharp brain, and moving fast, no time to stop for self-doubt.

And Castle, of course, is having a great time. Judge Markaway calls Montgomery to ask him what the hell is up with that.

"The dude was practically skipping when they came to ask me to sign their warrant," the judge says. "Hold on a minute. Fore!"

Roy waits until Markaway has taken his shot, and then replies, "Yeah, this case seems to have caught his interest. Not a big surprise since it was related to his books."

"Keep an eye on him, though, Roy. That kid has no sense of self-preservation."

"You noticed that too?" They laugh together and end the call.

Roy is delighted - over the moon - when Castle shows up again, the very next day after solving the Tisdale case, wanting to shadow Beckett as research for a new series of books. This is better than Roy could have possibly imagined. He has to work pretty hard to keep his poker face on, especially when he breaks the news to Beckett and she cries, "Oh no. No way." He bites the inside of his cheek, hard.

So they start working together, and it's great. They're solving cases and having fun. Roy is fully alert for any hint that their partnership is ... developing ... but it doesn't come. That's okay. He can be patient.

Castle invites Beckett along to the poker game at one point, which is interesting. As Roy had suspected, she does look a little intimidated at first, but she gets over it, and participates in the trash talk with plenty of snap and bite. So she doesn't manage to beat Castle in the final hand; oh well, you can't have everything.

At the end of the evening, Bob the mayor pulls Roy aside. "You set this up?" he asks, grinning. Roy still has his poker face on.

"Don't know what you mean, sir."

"Oh, sure. Sure you don't." Bob's grin widens. "Care to make a small wager?"

Roy allows himself the smallest of smiles. "Name your terms."

"A hundred bucks," says Bob, "those two hook up within a year."

"A year? Pssh," Roy scoffs. "Six months."

"Done." And they shake on it.

But six months go by, and while Beckett and Castle have had their ups and downs, essentially nothing has changed; they're still just working together, nothing more. Roy briefly considers the possibility that they're sleeping together and keeping it on the down-low, but eventually decides that it wouldn't be possible. Not for this long, not working as closely with the rest of the team as they do.

Reluctantly, he's forced to pony up to Bob, who proposes renewing the wager, but suddenly Roy isn't so sure, so he declines.

But not long after that, standing behind the window in his office, Roy watches them at the whiteboard discussing the latest case, and his eyes catch on Castle's face as Beckett turns to walk away. Roy watches Castle's eyes follow Beckett, and sudden realization strikes him so hard his mouth falls open.

He's in love with her. Castle, with Beckett.

There is no doubt in Roy's mind, not when he sees the way Castle looks at her when she isn't looking. The kid is completely, utterly, hopelessly smitten. Holy shit.

Then a serial killer starts targeting Beckett, calling her by her alter ego's name, and the feds blow in - and the killer blows up Beckett's apartment. In the midst of chaos, Roy spots another opportunity.

He goes about it subtly, again. All it takes is one offhand remark, in Castle's hearing but not directed at Castle, about Beckett needing somewhere to stay while she looks for a new apartment. Naturally, that seed takes root in the blink of an eye.

"It's the safest place in the city," Castle is saying a little while later in Roy's office, and Roy's poker face is holding firm while Beckett clings to her self-sufficient mask.

"Thank you, Castle, but I couldn't."

"You can, and you will," Castle says firmly, and Roy makes it an order. She hates it, but she'll go along. Thank goodness. He is really worried about her right now.

Roy trusts Castle not to take advantage of Beckett's emotional state - but then, there's a fine line between taking advantage and seizing an opportunity, and he also trusts Castle to walk that line. So he's feeling optimistic enough to call Bob and renew the wager.

But a few days go by, they catch the serial killer, the feds clear out, and Beckett finds herself a new place - and still nothing has changed. She and Castle are still keeping each other at arm's length. What the hell?

Another disastrous six months go by. Castle and Beckett are working together more effectively than ever, but she started dating some wet blanket from Robbery - another square-jawed, clean-cut, _boring_ law-enforcement boyfriend - and Castle took off for the summer with his ex-wife. The idiot!

Roy is at his wits' end. He pays up to Bob again and vows never to bet on his subordinates' personal lives again.

Castle comes back at the end of the summer, and of course, after much complaining, Beckett takes him back again. Shortly Roy learns that she has started dating some doctor. For God's sake, will these two ever get it together?

Roy keeps getting his hopes up, and they keep getting dashed. Castle and Beckett kiss to distract a guard so they can rescue Ryan and Esposito (Roy quietly redacts that section of the official report), but nothing changes. Castle still looks at Beckett like she's the sun, moon, and stars, whenever her back is turned - and now Roy notices that she looks at Castle in much the same way - but still nothing changes. They get locked in a freezer together - they save the city from a dirty bomb together - they travel to L.A. together to avenge Beckett's old training officer - and yet, somehow, unbelievably, they still aren't _together_ together. Christ Almighty, what the hell are they waiting for?

And then it all goes to shit. Roy's past, coming back to haunt him in the way that he supposes he always knew it would.

Roy Montgomery has been a cop his whole adult life, and he has seen some shit. Like all cops, he has thought about his own death. He's always imagined it coming at the hands of some lowlife scumbag; admittedly Hal Lockwood isn't exactly the scumbag he'd envisioned, but that's life for ya.

Like many cops, he has spent some time - mostly late at night, staring into a bottle - thinking about what he would want his last words to be. He's tried to craft some kind of poignant and bittersweet phrase that he might be able to remember in those final moments; something like _tell my wife I loved her with all my everything_ or similar. Hell, he's no wordsmith, but he thinks about it.

As it happens, though, Roy's true last words - muttered on a painful gasp into Kate Beckett's ear as she crouches sobbing over him on a cold hangar floor - are as inelegant and bitter as his life's end itself. "For God's sake, fucking kiss the man already," he chokes out. "You love each other." And he dies.

A year later, lying in a tangle of sweaty limbs, with her hair still dripping rainwater on Castle's pillow, Beckett finally tells him about Montgomery's last words. Startled, Castle thinks back - way back to those earliest poker games - and realizes, four years too late, how smoothly Roy bamboozled him into helping with the Tisdale case. Amazed, they talk it over and recall all the tiny ways in which Roy pushed them together, never once tipping his hand until the end.

They laugh about it together, and then Beckett turns her face to Castle's shoulder and cries. He wraps her in his arms and holds her while she mourns all over again for her lost mentor, her fallen idol.

A few years later, they bring little James Montgomery Castle to visit Roy's grave. They lay yellow roses and forget-me-nots beside the gravestone, and they stand arm in arm, looking at it, as the baby plays in the grass. "Sorry we took so long," Beckett says, and "Thanks for trying," Castle adds. Then they pick up their son and get back to work.


End file.
